This research is directed towards the synthesis of compounds considered to be potential bioreductive alkylating agents. Such molecules are viewed as undergoing an in vivo reduction which activates the formation of a potent alkylating agent. These in turn form covalent adducts with biologically important nucleophiles and thus exhibit biological activity as anticancer agents. The synthetic targets are all members of the naturally occurring quinine family. These are compounds which should undergo an in vivo reduction to a hydroquinine and these are amenable to an elimination reaction to give a reactive quinine methide, the biological alkylating agent. The specific compounds being synthesized are mitomycin, nanamycin and a series of analogs.